The 4 Biggest Mistakes Men Make on Dates

Before the onset of the COVID-19 pandemic, dating was a lot less complicated. Getting a first date could be ridiculously easy sometimes. I remember running a speed dating event where a woman decided to swipe on Tinder during a break. She ended up matching with a guy who was at a bar down the street, and she left her mini-dates in favor of a Tinder match! The dating world had almost too many options and chances to meet back then. Now, well, things are a lot different.

The lockdowns and social distancing norms have changed dating habits in fundamental ways. People take a first date more seriously during the pandemic because they don’t have as many social or dating opportunities as they once did.

Each date is important, so you need to make sure you are using all of your skills to give every meeting and interaction a greater chance of success. Look out for these four common mistakes men make on dates.

OK, let’s say you’ve successfully matched or met someone, and you are setting up your first date. You want to make sure you send the right signals by choosing a place she’ll like and doing something that will impress her a bit. You choose a fancy restaurant, get decked out in a suit, and share a meal while gazing into each other’s eyes. Sounds good, right? NO! The classic dinner date is a mistake if you’re looking to establish chemistry and get to know someone new.

The dinner date is ineffective because you have a table separating you from your love interest, and a server will frequently interrupt the flow of the conversation. That makes establishing physical touch via hand-holding or flirty gestures more difficult. It’s an restrictive environment where people adopt a formal dating persona.

Plato once commented that you can learn more about a person in an hour of play than in a lifetime of conversation. That’s still true today. So go do something on a first date! Even if it’s grabbing a cup of coffee or taking a walk. Watch how your date interacts with the world. Are they nice to people? Find times to gently brush hands or shoulders. Maybe find something to do with a little friendly competition. This is really going to tell you much more about the person than what they would tell you over dinner.

Likewise, be careful not to plan too big of a date if it doesn’t match your personality. I had a client who was a very nice, quiet accountant. He knew about the advantage of taking the woman to an interesting location for activity dates. So would take his dates to the NYC Trapeze School. This is a very cool place that is a lot of fun! The problem was that because he was a quiet individual, the date overshadowed him, the dater! Women would remember that they went on a really cool date, but couldn’t remember anything about the guy next to them. 

Personally, I always enjoyed shooting pool with a date. You can collaborate, compete, tease, make lots of physical contact, and joke around about balls, sticks, holes, and racks. Pool has lots of fun innuendos to play with.

Of course, it doesn’t have to be trapeze or pool. Find something fun, and go do that!

Obviously, you never want to be late. Most of us know this, but may not realize how important this detail is at the beginning of a relationship. Before the first date, you don’t know each other well and may have only exchanged a few messages. Trust is fragile or nonexistent at this point. Feelings haven’t yet been established. You are still learning how the other person operates and what is important to them. 

When you are late to your first date, it sends a couple of negative messages. A first dater’s first job is to figure out if a stranger is trustworthy. Trust is a huge thing in a relationship, and it takes time to build. If you tell her you’ll be somewhere at 8 p.m., and then show up at 8:15 p.m., you are undermining that trust as if you had lied to her. You said something and didn’t stick to it. I know it seems like a little thing, but at this point she only has a few little things to go on — and being late doesn’t speak well of you.

I have my own particular pet peeve with time, and tardiness Being late signals that you don’t respect the other person’s time. Tell me a time. I don’t care what it is — it can be 7 p.m., 8 p.m., 9 p.m., or 10 p.m. Any time is fine. Just tell me the time you will be there. I’m a very punctual person, so I want to know when to be ready. 

I once had a guy friend who would take an hour to get ready and would be an hour late. We once even had train tickets, and he was 40 minutes late, so I took the train without him. It’s important to respect people’s time and have the wherewithal to know how long it’s going to take you to get ready. If you show up late, you’re starting a new relationship on a broken promise. Be on time!

People love to talk about themselves so ask lots of questions! Just make sure they’re relevant to the conversation and the person. Men can make a mistake if they ask questions that have nothing to do with anything. It can seem forced or disingenuous if you’re just rattling off questions you prepared in advance. If you need inspiration for icebreaker questions, it’s okay to do some research, but don’t feel as if you have to stick to any list you find.

Look, everyone loves to have people ask them about themselves. But it has to be in a way that seems like you’re actually interested, not checking off questions from a list. My female clients have told me — many times — that a lot of guys are just firing off questions seemingly at random. As soon as the woman is done answering “Where do you live?” he moves on to “Do you have hobbies?” and then “Where do you like to travel?” or “What foods do you like?” 

None of these are bad questions, but asking them in succession gives your date the feeling you’re going down a checklist or treating a romantic evening as if it’s a job interview.

Instead of making that mistake, have a few open-ended questions that you want to ask, and bring them up organically with follow-ups and responses intermixed. In short, have a real conversation. When you ask a question, actually listen to the answers and come up with another related question. If you ask her where she wants to travel, and she answers, “Ecuador,” don’t just move on to the next question. Explore this answer! What about Ecuador makes you want to go there? Do you have any connection to Ecuador? Do you want to go to Ecuador with people or on your own? Don’t be afraid to go off script and improvise some questions that’ll make her think.

Let’s lay it out. This has been a super shitty year. I get it. Every single aspect of life got harder for everyone. Across the board, it was terrible. Plus, dating is hard even without a pandemic! But you’ve got to remember that first dates are supposed to be fun.

You can gripe about your bad experiences, emotional baggage, and hangups as the relationship progresses, but it’s a bad idea to start on a negative foot. Don’t talk about your dating woes. Don’t bitch about your ex. Don’t talk about how frustrated you are with work or politics. No one wants to go out with a Negative Neil or David Downer. Even when things are tough, it’s important to sweep away the bad stuff and create some positivity in your dating.

If you’re not in the right headspace to date right now, I get it. A lot of people, including myself, have taken this time to grow and work on ourselves. But if you are ready to date, make sure you get into the right mindset. Change your clothes after work, look up some positive news stories, memorize a joke or two, do something you enjoy beforehand to elevate your mood, maybe a little exercise to get the blood going. You, as the dater, need to take a hand in creating the best space to give yourself the most advantages for chemistry to find you.

This article could easily become a whole book on what not to do on dates. A lot of things can trip guys up sometimes or make them feel less confident when flirting with someone new.

Fortunately, a little guidance can go a long way. I’ve listed a few common mistakes that are easy to work on and change. Even during a pandemic, some dating rules and relationship etiquette tips don’t change. This cuffing season may have its challenges, but with a solid strategy single men can find success in “The Hunt for Bed October!”